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My style has definitely evolved over the years. In my 20s, I bought a lot of things on sale and was still figuring out what actually felt like me. I tried trends, owned every color of the J.Crew V-neck tee (remember those?), and didn’t put much thought into longevity or fit.
In my 30s, I started dressing more simply. I leaned into neutrals, paid attention to fabric quality, and edited my wardrobe down to what I actually wore. It was less about trends and more about building a practical base.
Now, in my 40s—with two young kids—I’m even more thoughtful. I want pieces that flatter my frame without necessarily highlighting everything. I gravitate toward looser, more polished silhouettes. I rarely wear two-piece swimsuits or open-back tops, not because I’m insecure, but because they don’t feel like me right now. I want to feel confident and comfortable, especially when I’m moving through a busy day filled with preschool drop-offs and toddler wrangling.
I also find myself reaching for blouses or tops with more structure or feminine details, rather than basic tees. I used to love a simple V-neck, but now I want something that adds interest to a look—like my favorite Tuckernuck tops that work just as well with jeans as they do with trousers. That said—this post isn’t about rules. If short shorts make you feel amazing, wear them. If you love a bold trend, go for it. The most important thing is that you feel like you.
How My Style Has Evolved Through the Decades
In my 20s: I bought what was trendy and what was on sale. I wore pieces that looked good on other people without knowing if they worked for my body or lifestyle. My closet was overflowing, but rarely satisfying.
In my 30s: I started editing. I realized I felt better in classic cuts, neutral colors, and breathable fabrics. I began building a wardrobe that was simpler but far more wearable.
Now in my 40s: I value timelessness and comfort. I want clothes that flatter my frame, feel good on my skin, and suit my actual life. Whether I’m headed to a playdate or dinner, I want to get dressed and feel like myself—without second-guessing anything.
Top 5 Pieces to Invest In
These are the wardrobe staples that truly earn their keep in my closet:
1. A well-fitted blazer
Structured but not stiff, a good blazer instantly pulls an outfit together. I wear mine with denim, trousers, and even over any of these casual dresses (that work for mom life too). It’s a go-to for days when I want to feel elevated without trying too hard. I love this double-breasted blazer and the Navy Diana Blazer– the gold buttons are fabulous.
2. High-quality denim
Denim is a daily staple for me, so I’m picky. I want a great fit at the waist and hips, no gaping, and a cut that flatters my frame. I rounded up my go-to jeans in this guide, and the best denim shorts for moms here. If you’re still hunting for your favorite fit, start there.
3. Polished, practical shoes
I’m all about stylish shoes I can actually wear all day—I rotate through all of these neutral and versatile sandals in the summer, sleek loafers or low boots in the cooler months, and a pair of classic (tested and approved) white sneakers that work with jeans and dresses. I don’t have time for stiff or overly delicate shoes anymore.
4. A feminine dress
A flattering midi dress is my go-to for everything from dinners out to preschool events. I love that it feels polished but not fussy—and it works just as well with any of these white sneakers or summer leather sandals. For seasonal inspo, I’ve shared favorites casual summer dresses and travel-ready options in my European outfits post, plus some stunning Tuckernuck dresses I wear on repeat.
5. A timeless trench coat
A neutral trench coat is a true capsule wardrobe staple. It works through spring and fall, adds polish to any look, and layers beautifully over lightweight sweaters or dresses.
If you’re looking for the best winter coats to that are both stylish and practical, I’ve got you covered in my roundup of the best winter coats for women.
Style Do’s
Do invest in better fabrics: Cotton, linen, wool, and cashmere hold up better and feel so much nicer to wear.
Do lean into feminine details: Think soft textures, subtle ruffles, or a tailored puff sleeve—those little things can elevate your everyday outfits.
Do simplify: A neutral capsule wardrobe doesn’t have to be boring. This 2025 fashion trends post breaks down ways to mix timeless style with subtle nods to current trends.
Do focus on comfort and confidence: You can look put-together without sacrificing how you feel. These cute, athleisure outfits are proof of that.
Do adapt to your lifestyle: I need pieces I can move in, bend down in, and still feel polished for a meeting or event. Bonus if it holds up at the playground and the office. The Charlie Shirtdress is one of those very amazing pieces for me.
Style Don’ts
Don’t follow trends just to follow them: If it doesn’t feel like you, let it go—even if everyone else is wearing it.
Don’t overstuff your closet: You’ll wear your favorite pieces over and over anyway. Curate intentionally.
Don’t ignore function: Style isn’t worth much if it doesn’t fit your day-to-day life. I’m not saying you need to wear leggings 24/7 (though I do love the Amazon leggings I rounded up in this post) , but if something constantly rides up or restricts your movement, it’s probably not a keeper.
Don’t underestimate the power of accessories: A structured bag, simple statement necklace, or great pair of sunglasses can make an outfit feel complete.
Final Thoughts
In your 40s, style becomes less about trends and more about self-awareness. What do I feel great in? What actually fits my lifestyle? What do I want to reach for over and over again?
The answers will be different for everyone. I’ve learned that my best outfits are the ones that feel like me—practical, feminine, and timeless. If that means a flowy dress with white sneakers, or a great pair of white jeans (I’ve rounded up the best white jeans after trying 15 brands in this post) with a detailed blouse, I’m in.
And remember—these are just my guidelines. Wear what makes you feel confident, beautiful, and at home in your skin. That’s the only “rule” worth following.
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